Synthesis and crystal structure of ((E)-{2-[(E)-(4-hydroxynaphthalen-1-yl)methylidene]hydrazin-1-yl}(methylsulfanyl)methylidene)azanium hydrogen sulfate monohydrate

Abstract

In the title mol­ecular salt, C13H14N3S+·HSO4 −·H2O, the protonation of the azomethine N atom in sulfuric acid medium involves the formation of a bis­ulfate anion. The mol­ecular structure of the cation is obtained from the thiol tautomer of thio­semicarbazone wherein the naphthalene moiety and the conjugation of the bonds contribute to the planarity of the mol­ecular skeleton.

Synthesis and crystal structure of (E)-2-({2-[azaniumylidene(methylsulfanyl)methyl]hydrazinylidene}methyl)benzene-1,4-diol hydrogen sulfate

“…This planarity is due to electron delocalization along the cation backbone, which is further stabilized by an intramolecular O13-H13Á Á ÁN5 hydrogen bond (Zhu et al, 2004). The bond ISSN 2056-9890 lengths and angles resemble those observed for similar thiosemicarbazone derivatives (Gangadharan et al, 2015;Joseph et al, 2004;Nehar et al, 2016;Houari et al, 2013). The anion (hydrogen sulfate) is disordered, split over two sets of siteswith relative occupancies of 0.501 (6) and 0.499 (6), and labelled with A and B suffixes.…”

Half-Sandwich Arene Ruthenium(II) Thiosemicarbazone Complexes: Evaluation of Anticancer Effect on Primary and Metastatic Ovarian Cancer Cell Lines

“…It is well known that thiosemicarbazones can show thione–thiol tautomerism due to the presence of the thioamide functional group ( Nehar et al, 2016 ; Zhang et al, 2009 ). S–C and C–N bond lengths have supported that both compounds appear in as a thione form.…”